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4‐( N , N ‐Dimethylamino)pyridine‐Embedded Nanoporous Conjugated Polymer as a Highly Active Heterogeneous Organocatalyst
Author(s) -
Zhang Yuan,
Zhang Yong,
Sun Ya Lei,
Du Xin,
Shi Jiao Yi,
Wang Wei David,
Wang Wei
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103028
Subject(s) - pyridine , chemistry , nanoporous , acylation , catalysis , conjugated system , monomer , covalent bond , polymer chemistry , organocatalysis , polymer , combinatorial chemistry , organic chemistry , enantioselective synthesis
We report herein for the first time the incorporation of a versatile organocatalyst, 4‐( N,N ‐dimethylamino)pyridine (DMAP), into the network of a nanoporous conjugated polymer (NCP) by the “bottom‐up” approach. The resulting DMAP‐NCP material possesses highly concentrated and homogeneously distributed DMAP catalytic sites (2.02 mmol g −1 ). DMAP‐NCP also exhibits enhanced stability and permanent porosity due to the strong covalent linkage and the rigidity of the “bottom‐up” monomers. As a result, DMAP‐NCP shows excellent catalytic activity in the acylation of alcohols with yields of 92–99 %. The DMAP‐NCP catalyst could be easily recovered from the reaction mixture and reused in at least 14 consecutive cycles without measurable loss of activity. Moreover, the catalytic acylation reaction could be performed under neat and continuous‐flow conditions for at least 536 h of continuous work with the same catalyst activity.